My roommate Jake was a great guy, but a slob. We never jerked off around each other, but it was very obvious that Jake was a very active jerker. Jake was a slob, and under his bed would amass a pile of cum filled tissues to the point where I would have to tell him to clean that shit up. Based upon the collection, I would say Jake was beating his meat on average 2 to 3 times a day. Definitely every morning when I would go to the shower, because sometimes I'd come back, and his 'tissue' hadn't quite made it under his bed, and on a couple of occasions, he would quickly roll over in his bed when I opened the door; when he obviously hadn't reached bliss before I returned. One Saturday night, we had both gone out to different parties, and when I got back to the room, I flipped on the light, and saw a sight to behold. Jake was passed out on his bed, his underwear around his knees, and his hand wrapped around a quite impressive boner. The idiot had passed out in the middle of whacking off. I did what any respectable roommate would have done, I whipped out my cell and took several pictures of him in his full glory.
The next day I tortured him unmercifully. He begged me to delete them, and I finally agreed. The next morning, I woke up, and looked over, and damn if Jake wasn't whacking away. I asked him what he was doing, and he sarcastically looked at me and said 'fuck you. Whats the point now. You've already seen me doing it, and I don't feel like waiting til you get your ass in the shower. Deal with it' and then he went back to jerking off. I decided to be the prick that I am, and started a play by play like I was watching a ball game. 'Jake STARTS TO dribble... looks left... Jake pulls the balls back... Jake appears winded, and this game is close to being over.... Jakes fakes.. Jake palms the balls... and with perfect timing 'JAKE SHOOTS... JAKE SCORES!' He then reached over his head, grabs some tissues, wipes the shit off his stomach, and tosses it under his bed, and calls me an asshole. I still had my morning wood, and decided WTF, and whipped my boy out, and started choking the chicken. Jake sat on the edge of his bed and watched me intently. It was really weird to have someone watch you get off, but also kinda hot. I ended up cumming pretty quick, and just as I shot onto my stomach, I heard the click of Jake's camera, and his loud cackling.
We actually jerked off quite a bit after that, not really doing it to thoughts of each other, just doing it like it was as natural as taking a nap.